Multicomponent synthesis of 4-aryl-NH-1,2,3-triazoles in the presence of Al-MCM-41 and sulfated zirconia

Article abstract of DOI:10.1016/j.tetlet.2017.05.055

The acid properties of Al-MCM-41 and sulfated zirconia were used to develop a strategy for the synthesis of 4-aryl-NH-1,2,3-triazoles via a multicomponent reaction involving various benzaldehydes, sodium azide and nitromethane. The efficiency of the process is analysed from the perspective of the difference in acids among the catalysts used.

Full text of DOI:10.1016/j.tetlet.2017.05.055

Accepted Manuscript
Multicomponent synthesis of 4-aryl-NH-1,2,3-triazoles in the presence of Al-
MCM-41 and sulfated zirconia
Blanca Ivonne Vergara-Arenas, Leticia Lomas-Romero, Deyanira Ángeles-
Beltrán, Guillermo Enrique Negrón-Silva, Atilano Gutiérrez-Carrillo, Víctor
Hugo Lara, José Antonio Morales-Serna
PII:
S0040-4039(17)30636-6
DOI:
http://dx.doi.org/10.1016/j.tetlet.2017.05.055
TETL 48948
Reference:
Tetrahedron Letters
To appear in:
Received Date:
Revised Date:
Accepted Date:
22 April 2017
11 May 2017
15 May 2017
Please cite this article as: Vergara-Arenas, B.I., Lomas-Romero, L., Ángeles-Beltrán, D., Negrón-Silva, G.E.,
Gutiérrez-Carrillo, A., Lara, V.H., Morales-Serna, J.A., Multicomponent synthesis of 4-aryl-NH-1,2,3-triazoles in
the presence of Al-MCM-41 and sulfated zirconia, Tetrahedron Letters (2017), doi: http://dx.doi.org/10.1016/
j.tetlet.2017.05.055
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Multicomponent synthesis of 4-aryl-NH-
1,2,3-triazoles in the presence of Al-MCM-41
and sulfated zirconia
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Blanca Ivonne Vergara-Arenas, Leticia Lomas-Romero, Deyanira Ángeles-Beltrán, Guillermo Enrique Negrón-
Silva, Atilano Gutiérrez-Carillo, Víctor Hugo Lara and José Antonio Morales-Serna

1
Tetrahedron Letters
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Multicomponent synthesis of 4-aryl-NH-1,2,3-triazoles in the presence of Al-MCM-
41 and sulfated zirconia
Blanca Ivonne Vergara-Arenasa , Leticia Lomas-Romeroa ∗ , Deyanira Ángeles-Beltránb , Guillermo
Enrique Negrón-Silvab ∗ , Atilano Gutiérrez-Carrilloa, Víctor Hugo Laraa, and José Antonio Morales-Sernaa
aDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. San Rafael Atlixco No. 186, Ciudad de México, C.P. 09340, México
bDepartamento de Ciencias Básicos, Universidad Autónoma Metropolitana-Azcapotzalco, Av. San Pablo No. 180, Ciudad de México, C.P 02200, México
ARTICLE INFO
ABSTRACT
Article history:
Received
The acid properties of Al-MCM-41 and sulfated zirconia were used to develop a strategy for the
synthesis of 4-aryl-NH-1,2,3-triazoles via
a multicomponent reaction involving various
Received in revised form
Accepted
benzaldehydes, sodium azide and nitromethane. The efficiency of the process is analysed from
the perspective of the difference in acids among the catalysts used.
Available online
2009 Elsevier Ltd. All rights reserved.
Keywords:
1,2,3-triazoles
Multicomponent synthesis
β-nitrostyrene
MCM-41
Sulfated zirconia
1. Introduction
azide. We propose to carry out this multicomponent reaction in
the presence of a solid catalytic material with acidic properties of
Given their structural characteristics, stability and
compatibility with various functional groups, 1,2,3-triazoles have
become a family of organic compounds of great interest for
various branches of chemistry.1 Their biocompatibility has
allowed them to be part of biologically active structures with
anti-HIV, anticancer, antibacterial, antiallergic and other
activities.2 Their stabilities at different pH values make them
attractive from the industrial perspective as corrosion inhibitors.3
the type Al-MCM-41 and sulfated zirconia (SZ). It is important
to emphasize that this reaction of three components has been
previously studied in the presence of homogeneous catalysts.14
However, it has not been studied in the presence of
heterogeneous systems, which is the main point addressed in this
work (Scheme 1).
The most common synthesis route to obtain 1,2,3-triazoles is
the cycloaddition reaction of an azide and an alkyne in the
presence of Cu(I) and Cu(II) salts (Huisgen reaction).4 However,
given the aforementioned interest, numerous methodologies
involving alternate sources of azides,5 alkynes6 and catalytic
systems have recently been described.
Among these synthetic alternatives, we find the addition of
NaN3 to β-nitrostyrenes to obtain 4-aryl-NH-1,2,3-triazoles.7
These triazoles are attractive for their biological activity,8 so
different research groups have developed various synthesis
protocols from mono-bromo alkynes,9 dibromo alkynes,10
semicarbazones,11 carbamates12 and β-nitrostyrenes.13
Scheme 1. Synthesis strategy for 4-aryl-NH-1,2,3-
triazoles.
Thus, the first step of this multicomponent reaction is the
With the idea of enriching these synthesis strategies, in this
work, we describe a protocol for obtaining 4-aryl-NH-1,2,3-
t—ria—zol—es starting from an aldehyde, a nitroalkane and sodium
preparation of a β-nitrostyrene in the presence of a heterogeneous
16
acid catalyst.15,
Subsequently, the addition of NaN3 to β-
nitrostyrene is carried out. This last step takes advantage of the
∗ Corresponding author. E-mail: llr@xanum.uam.mx (L. Lomas-Romero)
∗ Corresponding author. E-mail: gns@correo.azc.uam.mx (G.E. Negrón-Silva)

2
versatility of β-nitrostyrenes to act as excellent synthons in
various organic transformations,17 such as in the Michael
addition18 and the synthesis of vinyl sulfones,19 pyridines,20
Table 1. Textural properties of materials
Material
MCM-4130,31
1392.35
0.85
Al-MCM-4131 SZ16
BET area (m2/g)
Pore volume (cm3/g)
Pore size (Å)
1221.79
0.85
90.35
0.12
pyrroles,21
exo-4-Nitroprolinates,22
organofluorinated
compounds,23 halogenated dopamine analogues,24 substituted E-
alkenes,25 alkenylation of alcohols26 and furans.27
24.30
26.49
52.01
2. Results and discussion
2.1. Materials
An important part of this work is to observe the influence of
the acidity of the materials on the studied organic transformation,
and thus, it was necessary to determine the Brønsted acid and
Lewis sites present in MCM-41, Al-MCM-41 and SZ. This
analysis was performed by infrared spectroscopy at 80°C (Figure
3). Thus, in the infrared spectrum, it was possible to observe the
characteristic bands of pyridine coordinated to Brønsted acid
sites (1600 cm-1) and pyridine coordinated to Lewis acid sites
(1445 cm-1). The concentrations of both types of acid sites can
be estimated from the intensities of the bands at 1600 and 1445
cm-1. These results indicated a higher concentration of Lewis
acid sites in Al-MCM-41 and SZ than in MCM-41 (Table 2).16
This work began with the characterization of the materials.
First, the structures of MCM-41 and Al-MCM-41 were
confirmed by X-ray diffraction. Figure
diffractograms for MCM-41 (blue) and Al-MCM-41 (black), in
which reflections can be observed at 2θ = 2.2°, 4.0° in both
cases. These values are the same as those described in the
literature for these materials.28
1
shows the
1200
Al-MCM-41
MCM-41
1000
800
600
400
200
0
Table 2. Concentrations of acid sites of the catalystsa
MCM-41
1.36
1.41
81
Al-MCM-41
3.15
SZ
A.I. (Brønsted) mmol
A.I. (Lewis) mmol
Brønsted mmol/g
Lewis mmol/g
3.83
5.03
227
277
504
3.88
218
2
4
6
8
10
12
78
249
2 θ
Acidity mmol/g
159
467
a Calculated after desorption of pyridine at 80 °C.
Fig. 1. Diffractograms for MCM-41 (blue) and Al-
MCM-41 (black).
Figure
2 shows the diffractogram for SZ, where the
-0.2
-0.1
0.0
0.1
0.2
0.3
0.4
0.5
0.6
characteristic pattern of the tetragonal crystalline phase can be
observed, given by the reflections 2θ = 30.21°, 35.35°, 50.207°,
59.23°, 60.17°, 62.84°, 74.78° and 81.78°. Again, these values
are congruent with what is described in the literature.29
Table 1 shows the properties of the materials obtained by
nitrogen adsorption-desorption (BET method), allowing us to
compare the surface area and pore size of the catalysts. In the
case of MCM-41, the presence of the metal (Al) has no influence
on surface area or pore size. SZ shows a smaller surface area and
a larger pore size than MCM-41-type materials.
Al-MCM-41
ZS
MCM-41
1700
1650
1600
1550
1500
1450
1400
λ
Fig. 1. Pyridine desorption spectra for the different
catalysts
2.2. Catalytic activity
The next part of our work focused on studying the
condensation reaction of aldehydes 1a-1i and nitromethane
at 80°C by microwave heating in the presence of MCM-41
and Al-MCM-41, using DMF or toluene as the solvent, to
obtain the β-nitrostyrenes 2a-2i. The results shown in table 3
allow us to observe that the tendency of the reaction
catalysed by Al-MCM-41 is similar to the tendency
observed when the reaction is catalysed by SZ. As expected,
the yield is low when the condensation reaction is performed
25 30 35 40 45
50 55 60 65 70 75 80 2θ
Fig. 2. SZ diffractogram.

3
in the presence of MCM-41 without aluminium. The use of
piperidine as co-catalyst is determinant in the success of the
process because its absence within the reaction is reflected
in low yields, as previously described by our group.16
(Table 2) has a direct influence on the reaction yield, as
both Al-MCM-41 and SZ catalyse the cycloaddition more
efficiently than MCM-41.
Table 4. 1,3-dipolar cycloaddition of sodium azide to β-
Table 3. Synthesis of β-nitrostyrenesa
nitrostyrenesa
Yieldb
Al-MCM-
41
Yieldb
Al-MCM-
41
R=β-
nitrostyrenes
Entry
1
Product
MCM-41
SZ
Entry
1
R=Aldehyde
1a = H
Product
MCM-41
SZ
11c
8d
55c
65c
10c
12d
60c
70c
80d
2a = H
3a
51d
60d
2a
75d
10c
7d
57c
52d
70c
75d
12c
15d
84c
91d
87c
95d
2
3
2b = 4-Me
3b
3c
2
3
1b = 4-Me
2b
2c
15c
13d
68c
64d
72c
70d
10c
13d
79c
88d
88c
95d
2c = 3-OMe
1c = 3-OMe
2d = 3,4-Di-
OMe
17c
15d
73c
70d
80c
74d
4
5
6
3d
3e
3f
1d = 3,4-Di-
OMe
11c
15d
55c
62d
62c
70d
4
5
6
2d
2e
2f
2e = 3,4,5-
Tri-OMe
19c
12d
78c
75d
84c
80d
1e = 3,4,5-
Tri-OMe
10c
12d
65c
78d
73c
85d
1f = 6-
Bromopipero
nal
10c
7d
65c
60d
70c
74d
1f = 6-
Bromopipero
nal
11c
12d
57c
61d
66c
75d
10c
5d
70c
55d
70c
58d
10c
12d
78c
82d
85c
90d
7
2g = 4-Cl
3g
7
8
1g = 4-Cl
2g
2h
2i
10c
11d
77c
88d
88c
95d
10c
6d
65c
60d
60c
64d
1h = 2-Br
1i = Furfural
8
9
2h = 2-Br
3h
3i
5c
8d
75c
82d
88c
90d
18c
11d
77c
73d
81c
80d
9
2i = Furfural
a Reagents: β-nitrostyrene (1 mmol), sodium azide (1.2 mmol), material (50
a
Reagents: aldehyde (1 mmol), nitromethane (3 mmol), piperidine (0.1
mmol), material (50 mg). b Yield of isolated product after chromatrographic
purification. c DMF was used as solvent. d Toluene was used as solvent.
b
c
mg). Yield of isolated product after chromatrographic purification.
mixture of H2O-EtOH was used as solvent. d DMF was used as solvent.
A
After studying the condensation reactions (Table 3) and
cycloaddition (Table 4), we examined a multicomponent system
catalysed by Al-MCM-41 or SZ, which integrates both organic
reactions to obtain the 4-aryl-NH-1,2,3-triazoles 3a-3i. To
achieve this goal, we began with the synthesis of 4-aryl-NH-
1,2,3-triazole 3a from benzaldehyde, nitromethane and sodium
azide in the presence of piperidine and MCM-41, Al-MCM-41 or
SZ as catalysts. The reaction was carried out with microwave
heating at 80°C, using DMF as the solvent. Using DMF as the
solvent and SZ as the catalyst results in the best performance of
the multi-component reaction (85%). The yields of the reaction
decrease when Al-MCM-41 is used as the catalyst (70%). The
lowest yield is obtained when the reaction is performed in the
presence of MCM-41 (Table 5, entry 1). These results show that
there is a correlation between the acidic characteristics of the
material (Lewis and Brønsted acid sites) and the efficiency of the
material as a catalyst for the multicomponent reaction.
Subsequently, the 1,3-dipolar cycloaddition of sodium
azide and β-nitrostyrenes 2a-2i was performed to obtain the
4-aryl-NH-1,2,3-triazoles 3b-3i (Table 4). The reaction was
performed at 80°C with microwave heating, using DMF or
H2O-EtOH as solvents, in the presence of the catalysts
MCM-41, Al-MCM-41 and SZ. The testing was initiated
with the addition of sodium azide to β-nitrostyrene 2a in the
presence of MCM-41, obtaining triazole 3a with an 8%
yield using DMF solvent and 11% yield using a water-
ethanol mixture (Table 4, entry 1). Using Al-MCM-41 as a
catalyst, 51 and 55% yields were obtained using DMF
solvents and a water-ethanol mixture, respectively (Table 4,
entry 1). The yield increased when the reaction was
performed in the presence of SZ, with a 60% yield in DMF
and a 65% yield in a water-ethanol mixture (Table 4, entry
1). The tendency of the cycloaddition reaction to produce
the 4-aryl-NH-1,2,3-triazoles 3b-3i was evaluated with the
β-nitrostyrenes 2b-2i. From the results shown in table 4, it
can be deduced that the acid character of the materials
Finally, the multicomponent reaction was studied with the
aldehydes 1b-1i, which were reacted with nitromethane and

4
sodium azide in the presence of the catalyst systems described
above (Table 5). Again, the yields of the reactions are shown to
be related to the acidity of the materials (Table 2): the higher the
acidity of the catalyst, the higher the reaction yield.
the literature,32 a possible reaction mechanism is shown in
Scheme 2. The first step involves the interaction of the material
with the aldehyde 1a to obtain an activated intermediate I, which
may be immobilized in the interface solid/liquid. This
intermediate reacts with the piperidine to form intermediate II.
The next step is the condensation of II with nitromethane,
followed by the elimination of piperidine, allowing the formation
of β-nitrostyrene 2a. Finally, triazole 3a is obtained as a
consequence of the cycloaddition of sodium azide to β-
nitrostyrene 2a (Scheme 2).
Table 5. Multicomponent reaction to obtain 4-aryl-NH-1,2,3-
triazolesa
N
N
NH
N
O
+
H
+
CH3NO2 NaN3
Catalyst
DMF
R
R
1a-1i
3a-3i
MW, 80°C, 30 min
Yieldb
3. Conclusions
Entry
R=Aldehyde
1a = H
Product
Al-MCM-
41
MCM-41
15
SZ
85
In this work, we describe the use of heterogeneous catalysts to
develop a multicomponent system with the aim of synthesizing
4-aryl-NH-1,2,3-triazoles. The overall process involves the
condensation of aromatic aldehydes and nitromethane to obtain
β-nitrostyrenes, to which sodium acid is added, resulting in the
formation of triazoles. The quantification of the acid sites of the
catalysts MCM-41, Al-MCM-41 and SZ allowed us to conclude
that the acidity of the catalysts directly influences the
performance of each of the steps of the multicomponent process:
the higher the concentration of acid sites, the higher the yield.
1
3a
70
2
3
1b = 4-Me
3b
3c
21
18
80
72
90
91
1c = 3-OMe
1d = 3,4-Di-
OMe
4
5
3d
3e
21
17
71
80
92
90
1e = 3,4,5-
Tri-OMe
Acknowledgements
The authors would like to thank Consejo Nacional de Ciencia
y Tecnología (CONACyT projects: 239938 and 255819) for
financial support. BIVA is grateful to CONACyT for her student
scholarship. JAMS acknowledges support by the Royal Society
(UK) Newton Fellowship Alumni program.
1f = 6-
Bromopipero
nal
6
3f
15
75
86
7
8
1g = 4-Cl
1h = 2-Br
3g
3h
12
14
70
72
87
80
Supplementary data
9
1i = Furfural
3i
15
90
92
Supplementary data associated with this article can be found,
in the online version, at:
a
Reagents: aldehyde (1 mmol), nitromethane (3 mmol), piperidine (0.1
b
mmol), sodium azide (1.2 mmol), material (50 mg). Yield of isolated
product after chromatrographic purification.
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6
Highlights
• Multicomponent synthesis of 1,2,3
triazoles from aromatic aldehydes,
sodium azide and nitromethane
• Reusable
catalytic
heterogeneous
system
• Microwave assisted synthesis